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Identification of Some Constituents of Helicteres Guazumifolia Kunth

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Identification of Some Constituents of Helicteres Guazumifolia Kunth Journal of Pharmacognosy and Phytochemistry 2021; 10(2): 96-103 E-ISSN: 2278-4136 P-ISSN: 2349-8234 www.phytojournal.com Identification of some constituents of Helicteres JPP 2021; 10(2): 96-103 Received: 04-01-2021 guazumifolia Kunth (Malvaceae) leaves from Accepted: 19-02-2021 Sucre state, Venezuela Haydelba D’Armas a. Facultad de Ciencias de la Ingeniería, Universidad Haydelba D’Armas, Victoria Vásquez, Shailili Moreno and Gabriel Ordaz Estatal de Milagro, Milagro, Provincia de Guayas, Ecuador Abstract b. Laboratorio de Productos Some constituents of Helicteres guazumifolia Kunth leaves extracts, which were obtained by maceration Naturales y Lípidos, Departamento de Química, in petroleum ether and methanol, were proposed to separate and identify. Chemical separation was Universidad de Oriente performed by column and thin layer chromatography, while identification was done by Gas Cumaná, estado Sucre, Chromatography-Mass Spectrometric analysis (GC-MS) and 1D-2D Nuclear Magnetic Resonance 1 13 1 1 Venezuela experiments ( H, C, DEPT-135°, HMQC, HMBC, COSY H- H). Several fatty constituents were isolates from non-polar fractions of this Helicteres specie, such as: methyl cis-13-docosenoate, 1- Victoria Vásquez docosanol, and decyl decanoate. Other constituents were identified by GC-MS as 2-dodecanone, methyl a. Laboratorio de Productos hexadecanoate, butyl (2-methylbutyl) phthalate, ethyl hexadecanoate, n-eicosane, di (2-ethylhexyl) Naturales y Lípidos, phthalate, (22E, 24R)-stigmasta-4,22-dien-3-one, δ-stigmast-4-en-3-one, benzophenone, (4- Departamento de Química, methylphenyl) phenylmethanone, 6,10,14-trimethylpentadeca-2-one, dibutylphtalate, 4,8,12,16- Universidad de Oriente tetramethylheptadecan-4-olide, and cyclic 1,2-ethanediyl acetal (5α)-4,4-dimethyl-cholestan-3-one. Cumaná, estado Sucre, Results suggest that H. guazumifolia Kunth could biosynthesize several chemical families, including fatty Venezuela acid, hydrocarbon, terpenoid, steroid, and phenolic derivatives, which could suggest its possible b. Unidad Educativa Instituto ethnomedical uses. Libertador, Cumaná, estado Sucre, Venezuela Keywords: Helicteres, GC-MS, lipids, isoprenoids, NMR Shailili Moreno Laboratorio de Productos Introduction Naturales y Lípidos, Species of the Helicteres genus (Malvaceae, previously included in family Sterculaceae) are Departamento de Química, characterized by having distinctive fruits, which are spiral capsules composed of five Universidad de Oriente Cumaná, estado Sucre, unilocular carpels and may be ovoid to ellipsoid or subcylindrical (Golberg, 2009; Cowie, [1, 2] Venezuela 2011) . They are widely distributed around the world and their pharmacological potential has gained prominence, especially with H. isora and H. angustifolia that have a long history of Gabriel Ordaz use in traditional Chinese medicine; while about 149 compounds have been isolated from Laboratorio de Productos several of Helicteres species, including terpenoids, sterols, and phenolic compounds, among Naturales y Lípidos, [3] Departamento de Química, others (Fernandes et al., 2020) . Universidad de Oriente The specie H. guazumifolia Kunth is particularly abundant in several regions of America, such Cumaná, estado Sucre, as Mexico (Bravo et al., 2016; Notario et al., 2020) [4, 5], Costa Rica (Goldberg, 2009) [1], Venezuela Brazil (Fernandes and Oliveira, 2018; Stavis et al., 2020) [6, 7], Colombia (Angarita et al., 2014; Sanmartín-Sierra et al., 2016) [8, 9], and Venezuela (Lárez, 2007; Rondón and Cumana- [10-13] Campos, 2007; Fariñas et al., 2011, Díaz and Carrasco, 2014) . Population of these [14] regions seems to use this specie as medicinal plant (da Costa et al., 2020) , and although its ethno-botanical uses have not been indicated, they may be related to its effects on fertility and women’s health (Yazbek et al., 2016) [15]. Previous study of extracts obtained from aerial parts of H. guazumifolia Kunth showed slight antimicrobial and antifungal activities, and strong toxic activity against Artemia salina [16] (D’Armas et al., 2020) . Furthemore, it has been reported the chemical compositions of its leaves essential oil, which was constituted mainly by diisobuthylphtalate, pentadecanal, 2- Corresponding Author: chloroethyl linoleate, hexahydrofarnesyl acetone, and isophytol, among others (Ordaz et al., Haydelba D’Armas 2011) [17]. For that, the aim of this study was to isolated and characterize some phytochemical a. Facultad de Ciencias de la Ingeniería, Universidad constituents from petroleum ether and methanol extracts of H. guazumifolia Kunth leaves Estatal de Milagro, Milagro, collected in Sucre state, Venezuela. Provincia de Guayas, Ecuador b. Laboratorio de Productos Materials and Methods Naturales y Lípidos, Collection and identification of plant materials Departamento de Química, Universidad de Oriente Sample of H. guazumifolia was collected in the way between Cumaná city and San Juan de Cumaná, estado Sucre, Macarapana sector (10°38’44’’N, 63°02’20’’W; 43 mamsl), Sucre state, Venezuela. Venezuela ~ 96 ~ Journal of Pharmacognosy and Phytochemistry http://www.phytojournal.com Taxonomic identification was realized at the herbarium Identification by GC-MS was made by comparison of “Isidro Ramón Bermúdez Romero”, Biology Department, obtained values with those of WILEY and NIST databases, Universidad de Oriente, Sucre Campus, Venezuela. while assignations of chemical shift on NMR experiments were made by comparison with theoretical 1H and 13C NMR Extracts spectrums at Spectral Database for Organic Compounds Samples of dried and powdered H. guazumifolia Kunth leaves (AIST, 2017) [24], and NMR predictor available on-line were extracted with petroleum ether. Then, solvent was (Aires-de-Sousa et al., 2002; Steinbeck et al., 2003; Binev separated and evaporated under vacuum in a rotary evaporator and Aires-de-Sousa, 2004; Binev et al., 2004; Banfi and Heidolph (~11 mbar, 40 °C), obtaining crude petroleum ether Patiny, 2008; Castillo et al., 2011) [19-24]. extract (PEE). The vegetal residues were re-extracted with methanol. Solvent was separated and anhydrous sodium Results sulfate was added to dry (~5 g/100 mL of solvent). Then, Separation and analysis of fractions from PEE filtrated solvent was concentrated in the same conditions to According to yield and TLC analysis of the fractions from obtain crude methanol extract (ME). PEE, E2 and E3 were selected to be partitioned. Fraction E2 (157.9 mg) was chromatographed in column (silica gel 35-70 Separation mesh; petroleum ether-dicloromethane-ethyl acetate: 1:0:0, PEE of H. guazumifolia Kunth leaves (5.36 g) was 4:1:0, 3:2:0, 1:1:0, 2:3:0, 1:4:0, 0:1:0, 0:7:3, 0:1:1, 0:3:7, chromatographed in column (CC), using silica gel 35-70 mesh 0:0:1), obtaining 5 fractions (E2.1-E2.5, 96.39% w/w). as stationary phase in a relation in mass of 30:1 respect to Fraction E2.2 (58.6 mg) was separated by CC (silica gel 37- extract. Mobile phase was performed on basis to increasing 70 mesh, petroleum ether-dicloromethene: 1:0, 4:1, 3:2, 1:1, polarity with mixes of solvents in a relation in volume, 2:3, 1:4, 0:1) in 5 fractions (E2.2.1-E2.2.5, 87.37% w/w), starting with petroleum ether-dichloromethane (1:0, 9:1, 4:1, from which E2.2.5 (15.3 mg) was chromatographed by TLC 7:3, 3:2, 1:1, 2:3, 3:7, 1:4, 1:9, 0:1), then dichloromethane- (silica gel 60 mesh, petroleum ether-dicloromethene: 2:3), ethyl acetate (1:0, 4:1, 3:2, 1:1, 2:3, 1:4, 0:1), and finally ethyl obtaining 4 new fractions (E2.2.5.1-E2.2.5.4, 73.46% w/w). acetate-methanol (1:0, 4:1, 3:2, 1:1, 2:3, 1:4, 0:1). They were Fraction E2.2.5.2 (5.3 mg) was a white solid and showed to obtained 124 elutes, which were grouped in 15 fractions (E1- be a pure compound according TLC analysis (Rf = 0.26), E15, 2.35 g, 43.77% w/w). Thin layer chromatography (TLC) reason for which it was analyzed by NMR. on glass plates (20×20 cm2) covered with silica gel 60 mesh Chemical shifts are shown in table 1, which are consistent (0.5 mm) was used to join elutes according to separation with an unsaturated fatty acid methyl ester. The 13C-NMR observed under ultraviolet light and with ammonium spectrum of fraction E2.2.5.2 showed 15 signals, δC 174.30 molibdate solution (5% w/v) in aqueous H2SO4 (5% v/v). ppm corresponded to a quaternary carbon of the carbonyl Chromatography of ME of H. guazumifolia Kunth leaves group (C=O), δC 130.04-129.79 ppm were signals assigned to (5.08 g) was performed similarly with mixes of petroleum nucleus of a C=C bond (methynes, according to DEPT-135°), ether-ethyl acetate-methanol in a relation in volume of 1:0:0, δC 51.42 ppm was assigned to the primary carbon of the 4:1:0, 3:2:0, 1:1:0, 2:3:0, 1:4:0, 0:1:0, 0:4:1, 0:3:2, 0:1:1, methoxy group (-OCH3). Rocking methylene signals were 0:2:3, 0:1:4, and 0:0:1. It yielded 101 elutes, which were observed between δC 34.17 ppm and δC 22.72 ppm, and the grouped in 10 fractions (M1-M10, 3.16 g, 62.24% w/w). terminal methyl group appeared at δC 14.12 ppm of the 1 Continuous separation was performed by CC and preparative spectrum. Signals at δH 5.38-5.28 ppm (m) on the H-NMR TLC (1.0 mm of silica gel thickness). spectrum were assigned to the unsaturated protons, while the signal at δH 3.65 ppm (s) was attributed to methoxy protons. Characterization Chemical shifts around δH 2.28 ppm (t), δH 1.98 ppm (d), δH Some fractions obtained after a continuous chromatographic 1.60 ppm (s), δH 1.25 ppm (m) and δH 0.86 ppm (t), separation were analyzed by Infrared Spectroscopic (using a correspond to α-carbonyl methylene protons, α-methylene FTIR 16 PC spectrometer Perkin Elmer), Gas protons respect to double bond (α-CH2), β-carbonyl Chromatography-Mass Spectrometry (GC-MS, in a methylene protons, methylene protons of chain, and the chromatograph Hewlett Packard 5890 II with EI 70 eV, terminal methyl protons, respectively.
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